Phosphine Mediated Conjugation of S-Nitrosothiols and Aldehydes

Tyler D Biggs; Laksiri Weerasinghe; Chung-Min Park; Ming Xian

doi:10.1016/j.tetlet.2015.04.017

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Phosphine Mediated Conjugation of S-Nitrosothiols and Aldehydes

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Phosphine Mediated Conjugation of S-Nitrosothiols and Aldehydes

Tyler D Biggs, Laksiri Weerasinghe, Chung-Min Park and Ming Xian

Tetrahedron letters, Vol.56(21), pp.2741-2743

05/20/2015

DOI: https://doi.org/10.1016/j.tetlet.2015.04.017

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https://hdl.handle.net/2376/114204

PMCID: PMC4467916

PMID: 26089576

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Abstract

Thioazaylide

Thioimine

Conjugation

S-Nitrosothiols

Aldehyde

S-Nitrosothiols (SNO) and their biological implications as an important post-translational modification are under active investigation. In our work on bioorthogonal reactions of protein SNO we have uncovered chemistry of this functionality that shows synthetic promise. Herein we report a phosphine-mediated reaction between SNO and aldehydes to form thioimines. A simple synthesis of benzoisothiazole based on this reaction is presented.

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Title: Phosphine Mediated Conjugation of S-Nitrosothiols and Aldehydes
Creators: Tyler D Biggs - Department of Chemistry, Washington State University, Pullman, WA 99164, USA
Laksiri Weerasinghe - Department of Chemistry, Washington State University, Pullman, WA 99164, USA
Chung-Min Park - Department of Chemistry, Washington State University, Pullman, WA 99164, USA
Ming Xian - Department of Chemistry, Washington State University, Pullman, WA 99164, USA
Publication Details: Tetrahedron letters, Vol.56(21), pp.2741-2743
Academic Unit: Chemistry, Department of
Publisher: England
Grant note: R01 GM088226 / NIGMS NIH HHS
Identifiers: 99900547592501842
Language: English
Resource Type: Journal article